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A novel approach to the regioselective acylation of spirocyclicC-glucoside of papulacandins

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
21
Identifiers
DOI: 10.1016/s0040-4039(02)00664-0

Abstract

Abstract A novel approach to the regioselective acylation of spirocyclic C-glucoside of papulacandins is reported. Conditions were found to effect regioselective acylation of triol 2 to give 2- O-acyl derivatives ( 5 ), which after deprotection with TASF afforded exclusively 2- O-acyl derivatives ( 8 ). An extensive migration of the acyl group from 2- O- to 3- O-position was observed when the desilylation was conducted with TBAF. These findings provided with a convenient means for extending the SAR of papulacandins at these positions.

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